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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:02:03 UTC

Update Date

2021-09-26 22:57:48 UTC

HMDB ID

HMDB0247880

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(S)-3-(2-Methylphenoxy)propane-1,2-diol

Description

(S)-3-(2-Methylphenoxy)propane-1,2-diol, also known as mephenesin or 1-(2-tolyl)glycerol, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Based on a literature review a significant number of articles have been published on (S)-3-(2-Methylphenoxy)propane-1,2-diol. This compound has been identified in human blood as reported by (PMID: 31557052 ). (s)-3-(2-methylphenoxy)propane-1,2-diol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (S)-3-(2-Methylphenoxy)propane-1,2-diol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   11                                                       
CONECT    7    9   13                                                       
CONECT    8    1    4   10                                                  
CONECT    9    6    7   12                                                  
CONECT   10    5    8   13                                                  
CONECT   11    6                                                            
CONECT   12    9                                                            
CONECT   13    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0247880
HETATM    1  C1  UNL     1       0.439   1.150   2.191  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.434   0.749   1.170  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.737   1.160   1.342  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.661   0.788   0.394  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.270   0.018  -0.700  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.945  -0.381  -0.843  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.024  -0.008   0.105  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.302  -0.375   0.014  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.731  -1.158  -1.086  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.210  -1.448  -0.996  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.433  -2.140   0.183  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.932  -0.100  -0.926  1.00  0.00           C  
HETATM   13  O3  UNL     1      -4.293  -0.253  -0.759  1.00  0.00           O  
HETATM   14  H1  UNL     1       0.958   1.203   3.170  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.374   0.400   2.301  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.025   2.157   1.991  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.050   1.752   2.177  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.707   1.083   0.475  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.023  -0.244  -1.406  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.668  -0.984  -1.710  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.169  -2.081  -1.216  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.546  -0.530  -1.995  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.555  -1.975  -1.898  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.589  -1.525   0.949  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.477   0.429  -0.052  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.690   0.477  -1.841  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.639  -1.138  -1.034  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    7
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8
CONECT    8    9
CONECT    9   10   21   22
CONECT   10   11   12   23
CONECT   11   24
CONECT   12   13   25   26
CONECT   13   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2-Tolyl)glycerol	ChEBI
1-(O-Tolyl)glycerol	ChEBI
Mephenesin	ChEBI
Tolserol	Kegg
Kade brand OF mephenesin	HMDB
Sanofi synthelabo otc brand OF mephenesin	HMDB
Dolo visano m	HMDB
Décontractyl	HMDB
Mephenesin kade brand	HMDB

Chemical Formula

C₁₀H₁₄O₃

Average Molecular Weight

182.219

Monoisotopic Molecular Weight

182.094294311

IUPAC Name

3-(2-methylphenoxy)propane-1,2-diol

Traditional Name

mephenesin

CAS Registry Number

Not Available

SMILES

CC1=CC=CC=C1OCC(O)CO

InChI Identifier

InChI=1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3

InChI Key

JWDYCNIAQWPBHD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Toluene
Alkyl aryl ether
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.96	ALOGPS
logP	1.01	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.82 m³·mol⁻¹	ChemAxon
Polarizability	19.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	137.727	30932474
DeepCCS	[M-H]-	134.602	30932474
DeepCCS	[M-2H]-	171.378	30932474
DeepCCS	[M+Na]+	146.916	30932474
AllCCS	[M+H]+	140.9	32859911
AllCCS	[M+H-H2O]+	136.8	32859911
AllCCS	[M+NH4]+	144.8	32859911
AllCCS	[M+Na]+	145.9	32859911
AllCCS	[M-H]-	141.4	32859911
AllCCS	[M+Na-2H]-	142.4	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-3-(2-Methylphenoxy)propane-1,2-diol	CC1=CC=CC=C1OCC(O)CO	2186.5	Standard polar	33892256
(S)-3-(2-Methylphenoxy)propane-1,2-diol	CC1=CC=CC=C1OCC(O)CO	1547.5	Standard non polar	33892256
(S)-3-(2-Methylphenoxy)propane-1,2-diol	CC1=CC=CC=C1OCC(O)CO	1593.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol EI-B (Non-derivatized)	splash10-0a4i-5900000000-3ce39ed63d61e07d52b5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-b7efb73b226cd03e49fa	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Positive-QTOF	splash10-001i-1900000000-931c8271d6fb5643cfc9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Positive-QTOF	splash10-069r-5900000000-2cb0895d9a4b0640f61f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Positive-QTOF	splash10-0a4i-9200000000-78c2e6485ea71c262216	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Negative-QTOF	splash10-053r-0900000000-0a6d1982ba1d3a0753e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Negative-QTOF	splash10-0a4i-1900000000-608832f5bcea0fe354e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Negative-QTOF	splash10-0a4i-9700000000-bee7aa8f073d3e740ef7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Positive-QTOF	splash10-0a4i-2900000000-89f2644627652f40004f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Positive-QTOF	splash10-0a4l-9300000000-6e1a77602ee5ab89b163	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Positive-QTOF	splash10-0006-9000000000-bb8f781584ee22fd2df4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 10V, Negative-QTOF	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 20V, Negative-QTOF	splash10-0a4i-9300000000-8864c588d454f239c30a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-(2-Methylphenoxy)propane-1,2-diol 40V, Negative-QTOF	splash10-0a4i-7900000000-ed674141cf39eafe84a2	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13583

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00052346

Chemspider ID

3919

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mephenesin

METLIN ID

Not Available

PubChem Compound

4059

PDB ID

Not Available

ChEBI ID

94398

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (S)-3-(2-Methylphenoxy)propane-1,2-diol (HMDB0247880)

MOL for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

3D MOL for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

3D SDF for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

3D-SDF for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

PDB for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

3D PDB for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

SMILES for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

INCHI for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

Structure for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

3D Structure for HMDB0247880 ((S)-3-(2-Methylphenoxy)propane-1,2-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra